


Singer's Rump

by MoonlightIcarus



Category: Supernatural
Genre: Anal Gaping, Ass Play, Barebacking, Begging, Body Hair, Body Worship, Crack, Creampie, Dom Crowley (Supernatural), Dom/sub Undertones, Enemas, Established Relationship, Facial Shaving, Filthy, Hair Kink, M/M, Manipulation, Mildly Dubious Consent, Oral Sex, Orgasm Delay/Denial, Smut, Spanking, Sunburn, Top Crowley (Supernatural), Underwear Kink, Underwear Theft, Wax Play
Language: English
Status: Completed
Published: 2019-11-05
Updated: 2019-11-13
Packaged: 2021-01-23 18:37:13
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 9,509
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21324796
Author URL: https://archiveofourown.org/users/MoonlightIcarus/pseuds/MoonlightIcarus
Summary: Crowley has always had an appreciation for a nice big hairy ass and Bobby has a perfect one to play with.Here's how the fascination progressed over time.
Relationships: Crowley/Bobby Singer
Comments: 7
Kudos: 36





	1. Chapter 1

**Author's Note:**

> This work just popped into my head and I had to right it.

Crowley had never understood the appeal of shaving your body hair. Maybe it related to being born back before such things were available to the common folk but he was a fan of course rough hair covering someone's skin. He liked the added visual detail from after he fucked someone good, rucked up sweaty hair meant a job well done. It was one of the reasons why after he first saw Robert Singer wanted the man all to himself.

....

(First time)

Getting the hunter to agree to bottom for him was easier than he anticipated and he didn't need to resort to magic or coercion to do it. The hunter just claimed that he was pent up and went ass up for him, claiming it wasn't his first time with another man. 

That should have reassured Crowley in his plan but instead it angered him. While Bobby stripped down in front of him he just thought of all the souls he would torture personally for laying a hand on what was his. Bobby had set himself up on the bed laying on his stomache with his legs spread slightly. Crowley snapped his clothes away and climbed up behind the body on the bed, he took a long look at that bare ass for the first time. It was exactly what he had hoped it would be, big and plump pale flesh covered in hair with an pink little pucker that would stretch out around him wonderfully.

He pulled that lowed body up so he could fuck it while he was on his knees on the bed, leaving Bobby in a perfect position of submission. It also meant that the hunter wouldn't be getting any friction until he said so. 

Crowley placed a hand on each of those cheeks and squeezed them tightly, enjoying the moan the man under him was eliciting. He prepped the hunter with a little magic, spread his ass wide and pushed in all the way. He wasn't going easy on him, wanting to erase the memory of any man who he had been with previously, and drive home the fact of who really owned this ass. His hands were going to leave marks where they were gripping his thighs, as they should.

Twice Bobby had attempted to reach down so he could touch himself and both times Crowely had growled out a commanding no and the hand was retracted. The thrusts grew harder as it went on and if he got any rougher the headboard would start to crack the drywall behind it. The cries for friction became desperate right around the time Crowley felt himself close to cumming and he decided that he would touch Robert as soon as he was finished laying claim to his ass. Soon he achieved his orgasm, leaving his semen inside that ass and he reached around that stocky body to give two firm strokes to that torso.

They collapsed on the bed and Crowley held the other man close during his afterglow. 

....

(Naked in Bed)

After their first time Crowley realized how disappointing it was to watch Robert cover himself after sex and he needed to change that. All it took was cleaing them up with his powers and holding the human close to him in his iron grip until he gave up on the idea of getting out of bed and just slept naked against him.

For the days when they didn't have sex he would always sleep naked and turn up the heat so that Robert would be too hot to keep his clothes on. The first night he did it the hunter made no change but the second he went to bed in a wifebeater and boxers instead of a tee shirt and sleep pants. It wasn't what he wanted but it was closer so he turned the heat up more. He was careful to only do it in the bedroom with his powers so if Robert did check the thermostat he wouldn't know what was wrong. He went down to just a pair of briefs for two nights and woke up with sweat dripping down his balls in the morning, at first it appeared that he would spend a third night like that but after an hour in the heat the briefs fell to the floor and Crowley spent the night stairing at the exposed skin instead of sleeping. 

He made such a habit of it that even on nights when Crowley wasn't manipulating the temperature of the room he would strip down to nothing before going to bed. As it transitioned to the colder months of winter he tried to sleep with clothes on again but was unable to get comfortable and slept nude even then. On nights Crowley was there next to him he would always curl up close to him, by then Crowley wasn't even changing the temperature at all.

....

(Tanning)

As the Winter gave way to Spring and eventually Summer Crowley had another way of enjoying Robert's ass, sunbathing. He had convicted the hunter by claiming he needed some vitamin D and that some time outside relaxing would do him good. That had been the easy part, the difficult part was convincing him to wear a thong to soak up the sun in. 

When Bobby had protested that he would look like a fool Crowley only had to argue that they would be on his private property the entire time and that the only person who ever even saw him naked was Crowley so the hunter should humor him this once, as well as promising more sex if he said yes. He regrettingly agreed to do it and slipped on the white shear thong. It was small and barely covered any of his skin, part of his balls were visible, the outline of his dick was clear as day, and you could see right through it but Bobby knew he had to pick his battles and Crowley would only argue the same points as before if he challenged him.

Crowley wore an identical article of clothing and as they stepped onto the covered back porch Crowley lead him over to a clearing in the back lot where two chairs had been set up that would allow the sun to hit them constantly.

Once they made made it over to the set up Crowley offered to help him apply his sunblock so he didn't burn and Bobby agreed to let him do it. The demon allowed his fingers to dance over every hair on that body as he massaged the sunscreen into his skin more thoroughly than necessary. He got areas Bobby himself could have reached easily and even got under his Thong and around his dick, claiming that he was being thorough when protests arose. Eventually his front was finished and he turned over to let Crowley do his back for him. He was just as invasive as before but he had a little trick planned when he got to that ass. He swapped out the sunblock for extra strength tanning oil so that his ass would turn a deliciously bright red in the sun, even getting the area between his cheeks and getting his hole as well. Bobby didn't even argue with it because he was half asleep by that point, soon Crowley finished and he took his chair next to him, always appreciative of a good view. He could see the way that ass bulged out from the slope of his back and its plump curve fell over his thighs and how it was all gleaming in the sunlight.

Every hour he would remind the human to turn over and he enjoyed every little peak he got at that slowly burning ass. For thirteen hours they stayed out in the sun stopping every four to reapply the sunscreen and tanning oil. By the end of it Bobby's ass was just a shade away from fire engine red just as Crowley had hoped. Things could go two ways from here Bobby could continue life as usual and flinch with every step as his ass rubbed against his underwear and Crowley would be the only one who knew why, or he would go around bare assed while he healed up, giving Crowley a long term view of it. Close to the end when Bobby was laying on his back he started to look uncomfortable just like he should be, and when he turned over I to his stomach again Crowley used an excessive amount of oil and left him like that for two straight hours before the sun was fading too much to be useful to him.

When Bobby questioned why only that had been burned he made the excuse that it had never been exposed to sunlight before so it was the most vulnerable part of him. The reasoning was believed and the hunter began formulating how to deal with his issue and Crowley suggested his more risque idea. After some coaxing he got Bobby to go with the option and soon he was walking around his house in a tight tee shirt that didn't hang low and brush his ass and a jockstrap that left everything on display. He had started laying down on his stomache with his legs spread out so his burned cheeks wouldn't rub against one another. There was the downside that they couldn't have sex but they exchange plenty of blow jobs in that time to make up for it. He could tell Robert was getting better at sucking cock each time he went down on him, what used to be simple kitten licks and the occasional swallowing had advanced to deep throating and holding him down while swallowing around the head. He managed to make the demon's body quake with the force of his release but he still struggled with swallowing it all down, but that would come with time as well.

The best part was something Bobby had initiated himself. He asked Crowley to help apply aloe to his ass since he couldn't see it himself. Crowley, being a good boyfriend, had agreed to do it as much as needed, that happened to be several times a day since he used the weakest lotion he could find and Robert came back to him again and again asking for him to apply another coat of it. He even was given permission to do it at night which he adored because he liked to watch the hunter squirm in his sleep while his ass was being poked and prodded. The way he would rub the aloe into his sensitive skin may have brought on more pain than relief but he was never told to stop so he continued it that way, he even managed to slip a slick finger into that hole when he was getting it, under the pretense of not knowing how deep the sunburn went. It was almost a shame he didn't get to enjoy the tan along the rest of that body with how preoccupied he was with his ass.

....

(Spanking)

He would never forget the first time he had gotten Bobby bend over his knee and spanked that hairy ass of his. It had been a few weeks after the sunburn incident. Bobby was angry because he claimed he no longer needed Crowley to smear cream on his ass and Crowley said it was still healing. Truthfully his ass had been fully healed for three days at the time of the argument, but Crowley wanted to milk the opportunity as much as be could.

Bobby lacked any real intimidation standing around in just a shirt and a jockstrap but when he started to swear more than usual and make threats of an exorcism he decided to act. Faster than the man could react Bobby was over Crowley's knee with one arm preventing him from getting up and another spanking his ass like a bratty toddler.

Crowley kept up a hard assault on that freshly healed skin. He continued through the angered shouts and protests, past the frenzied bargains, and the pathetic apologies that were begged from between those gasps and means that came from those chapped lips. His hand would never grow sore but he was going to make sure that that ass was, he got every side and angle in his litany of hits, being a true perfectionist when it came to a proper punishment.

After that ass was as red as it had been after their day in the sun he finally ceased the onslaught and asked Bobby who was in charge. When he didn't receive a response he spanked over this hole a few more times until he cried out that Crowley was in charge. 

He was satisfied with the answer and address the hunter in a tone of pure authority and control. "Good, now there are going to be some changes around here, you clearly don't know what's good for you and I do. You're arse may have been healed but, because you made a fuss about my opinion it's all red again. If you listen to me things like this won't happen." After seeing a frantic nod from that head that was dooping on the bed be continued. "I expect you to apologize by sucking me off, I wanted to have sex without but you ruined that, so don't fuck this up too."

As soon as he was released Bobby scrambled to the floor and flinched when his bruised ass rested against his heels. He pulled Crowley's hard dick out of his briefs and sucked him down in the most desperate blow job Crowely had ever received. Thankfully Crowley wasnt judging him on the quality of it and he even swelled all the cum without being told to do so.

From then on that's how their days went. Crowley would spank him for doing something that pissed him off or just as a reminder of who was in charge of their relationship. It made Bobby much more agreeable to Crowley's suggestions, and who would have thought all it took to make a hunter his bitch was knowing how to give a good proper spanking.

....

(Wardrobe)

He had been beating Robert's arse for three days and it was time to make his first major change of how things worked around the house. He had exchanged all the clothes in his closet and dresser with some more fitting attire. It was now only jockstraps, tight fitted shirts that would stretch over his torso, and short sleeveless flannels that had the buttons removed so he couldn't button them up and hide his body behind poorly fitting clothes anymore. Somedays he planned on having the hunter go around in just a shirt and nothing on his lower bod, but that would come later once the new rules of the house had been accepted.

The complaints from Robert were silenced by another spanking and the threat of no orgams for two days. Robert was fresh put of the shower and his towel had been ripped away and after several swats the issue was settled. He had even been kind enough to allow Robert to wear normal clothing if he needed to go out or have company over.

He also made the important decision that Bobby had been missing out on proper exercise and mandated it for him daily. Specifically several dozen squats to tighten up that ass and build the strength in his legs so he would be better at riding Crowley's cock.

"It was important to develop these skills even late in life," he claimed when Bobby started questioning him. He didn't ask any other questions and Crowley choose not to punish him since he was behaving and learning to listen properly.

His effort was visible after several weeks. That ass was more pronounced and stretching against the bands of his jockstraps. There was so much jiggle with every step and most times Bobby was unable to walk between rooms without his ass getting groped by those warm hands. He also tested his stamina and found that the hunter could ride him straight through to the end of his afterglow so long as Bobby wasnt allowed to get off during it. That was fine because he intended to discipline the man into understanding that Crowley was the one in charge of when he got to cum.

Later the tee shirts were replaced with sheer crop top shirts that were made of the same material as sports jerseys. They left nothing to the imagination but Crowley found the hunter more obscene when he was wearing such revealing clothing rather than just purely naked, though he did make sure the hunter was nude in bed overnight for their regular fucking.

He was slowly convincing the hunter that he didn't know what was best for him but Crowley did. He reaffirmed his lessons with nice rough sex when he saw behavior he approves of. Robert had seen sex as a reward for good behavior and an orgasm as something he only recieved for going above and beyond. Soon he had the hunter deferring to him for making all decisions and didn't question his authority when new rules and regulations were given to him, because he believed he was unfit to take care of himself and he looked to Crowley for that.

...

(Morning Routine)

The way he spend his morning had changed slightly in the past few months. First he was woken up by Crowley delivering his morning spanking. It would be any number that Crowley deemd fit that day to reassure Bobby knew who was in control. Afterwards he would put on two nipple pumps to keep them nice and plump where they would poke out against his shirt. Then he would go to the bathroom and start his liter enema at the slowest speed possible. Crowley had started it when he realized how ineffiecnt it was to clean him out whenever he wanted to fuck him so he had him do it every morning so any impromptu sex was good to go. It normally took about 20 minutes for all of the water to work it's way inside of him inside of him and no matter how often it happened he was always left aching and cramping but it was necessary to do it daily to stay healthy. Once it was all inside of him he would remove the nipple pumps and make sure they were big enough. After that he held the water inside of him during his morning shower. He was expected to wash himself thoroughly and that meant taking his time and letting the enema do is work inside of him. Once he was clean he was allowed to let the enema out into the toilet. Then he used a single placket of lube to work all five fingers into himself. It was finished up by doing the number of squats Crowley requested that day, sometimes he could barely make it to his dresser because he had done so many of them but he had to get dressed like Crowley expected him to.

The days diverged from there. On normal days he would get dressed and go about his chores to keep the house in order. If he needed to do research he would always find Crowley sitting in his desk chair with his cock out. Bobby would need to sit on it while he worked to keep it warm and prove he wasn't neglecting Crowley. It was always hard to focus with a dick so deep inside of him but he was good and he worked through it. Things got harder when Crowley toyed with his swollen nipples but he tried to keep working until he eventually gave up and started riding that cock. He didn't get to cum during it but the feeling of Crowley's semen dripping from his gaping hole after it was more than enough of a reward and his nipples would be aching for the rest of the day as another reminder of how good he was. 

On other days he's would have clenching days. On those days once he had stretched himself out he would squat over a dildo and then clench around it before standing up so I would stay in there. This was done to make sure his hole never got too loose, there was a fine line between sloppy and sexy. On clenching days he couldn't work in the library because he couldn't sit on a cock. He would need to keep the dildo in his ass until Crowley decided to pull it out at some point during the day, and fuck him to see if he was tight enough. If he was then the dildo was removed for the day and everything went on as it normally would. If Crowley deemed his hole too loose he would recieve a spanking before the dildo was put back inside of him and Crowley would try again later that night. If he was tight enough that night then Crowley would fuck him and they would go to sleep. If at any point he dropped the dildo because he couldn't hold it in right his ass was spanked and they would try again that night.

The worst days were the ones when he failed again at night with the dildo. When that happened Crowley didn't fuck him and he would get an ass whooping with a belt instead of a hand. The next day his morning spanking was replaced with another turn with the belt and he wasn't allowed to give himself an enema or stretch himself out. He always felt horrible on those days because he failed and he didn't make Crowley happy. It made his chest ache and his hole hurt from being so stopped up. Whenever a day like that happened he would always cave and beg for Crowley to fuck him but Crowley was a good man and always denied him, because he knew what was best for Bobby. 

Once the night came Crowly would open him up himself and it always made shame run through his veins, because he should have been able to do it himself but he wasnt good enough. He was lucky to have someone as forgiving as Crowley be in charge of his life because he made far too many mistakes and the demon was helping him learn to make less. 

After Crowley had finished fingering his ass he would test him again to see if he was tight enough. Evertime he had said it was good except for once. That time Crowley said he would need another full day to tighten up and it had been horrible. From the moment he woke up he was begging Crowley for forgiveness and he didn't even make it to lunch before Crowley had him thrown over his knee and given him the worst beating he had ever experienced, because he was being a brat. He made sure to do his absolute best so it would never happen again, and so far he had been getting better and better at obeying and following orders like he should. 

....

(Juliet)

That brings him to today where he just finished fingering his ass open and he donned a white jockstrap that had been discolored from all the cum stains on it and a matching while tank top made from a shear fabric that his nipples stood out against. He glanced out the window and saw small white flakes fluttering down from the sky. He was glad that he wouldn't have to go outside because the cold wouldn't feel good on his exposed skin.

Bobby decided to make a casserole for breakfast as a thank you since Crowley would have to go outside an and get the mail for him. Normally he would do it (getting the mail was the only time he ever wore shoes, usually some sandals or flip flops). He would put some shoes on and go out as he was to the mailbox. Starting out he had been self conscious about it, but that faded the more he trusted Crowley like he should have from the beginning. Even cold didn't bother him too much but snow was beyond the realm of possibility. He made it to the kitchen and started getting everything ready.

He was bending over to stick the dish in the over and had just closed it when the cool air against him was replaced with what felt like a long rough tongue licking across his ass and tickling his hole. When he turned around expecting to see Crowley he was greeted by nothing at all. "Crowely." He called. "Crowley. He was louder this time.

"Yes. What is it love I was getting the-" he had just walked into the kitchen with letters in his hand before tossing them onto the table and making a gesture like he caught a huge dog that jumped into his arms. "I see you found Juliet."

"Juliet?"

"Yes she's one of my hell hounds. Was she giving you any trouble love?" He looked like he was struggled to hold the dog Bobby couldn't see.

"Uhm..not really but well...she did lick my ass for some reason." He was no stranger to someone licking his hole but usually it was Crowely himself not one of his pets.

"Well than makes sense because Juliet is a special hell hound who was trained to find things that belong to me."

"Oh, okay. That makes sense." It was a good thing Crowley owned his ass because Bobby wouldn't know how do take care of it right on his own.


	2. Chapter 2

**Summary for the Chapter:**

> Some finer point of how things developed.

(Shaving)

He had plucked the razor from Bobby'shand before he could bring it up to his face to shave.

"Were you planning on giving this back to me?" His beard was getting a bit too bushy for his taste and it was time to trim it.

**"No, but I'd gladly do the job for you. Unless you feel like arguing and I can tell you that will be the hard way.**

**Crowley had been spanking his ass to get him in line for several days now and he would prefer to avoid any unnecessary pain if it could be avoided. He already got one round today from complaining about his clothes again. He was over Crowley's knee and he dropped the issue shortly after it.**

**"Fine but don't try anything."**

** U]i"I would never." SNAP**

** _. A small wooded stool had appeared in his bathroom next to where Bobby was standing. "Take a seat love."_ **

** **

** _He did as told and tied not to flich at the feeling of the wood agaisnt his sore exposed bottom as he waited for Crowley to start. The razor that had previously been in his hand was replaced with one of the single straight blades most barbers would use. It was brought up to his neck and Bobby drained his head away before a small slice was made across some of the hairs around his neck. He never quite stopped being tense but he allowed the demon to continue without much fuss. He only got around the bottom of his neck and a bit at the top of his cheeks before banishing the blade from existence._ **

** **

** _"Aren't you forgetting something?" There was still hair tickling his lips and it felt too thick all around his face._ **

** **

** _"Just a moment love." He brought a comb up to his face and began to straighten out all the frizzy hairs and patches along his beard. When it had all been straightened out it hung across his mouth even made and he was tempted to start bitching when Crowley brought two oil coated hands up and started styling it all. His beard was tucked and folded over the patchy areas of it and the hair of his mustache was pulled aside out of the way. "Take a look."_ **

** **

** _His turned around and his reflection was so different from what he was used to. His beard was perfectly styled and shaped and he had been given a handlebar mustache on top of it all. It was definitely different, but he kinda liked it._ **

** **

** _"I'll be honest I did this because it makes you look sexy and I'm going to adore the way it feels when you suck my cock."_ **

** **

** _He was somehow still shocked at the declaration even after all they had been through. Crowley had come up to him from behind and just patted at his still red ass. "Why don't you get down and let me see how it feels. If you'd rather not I can always make this fine arse burn again and then fuck you while it's still raw."_ **

** **

** _Bobby turned and dropped to his knees with a thud that couldn't be healthy for someone of his age. It was fortunate that Crowley had forgone clothing so early in the morning so all Bobby had to do was place his hands on that ass for leverage and sing down onto that long cock all the way to the base._ **

** **

** _When he attempted to pull off to take deep breath he was stopped by the hand on the back of his head holding him in place. "Now love I know you can give a good blowjob but we need to start working on holding your breath for longer and keeping my cock warm. I wont let you get hurt but you need to trust me when I'm teaching you, so get comfortable because you have so much to learn._ **

** __ **

** __ **

....

(Orgasms)

In the beginning he had to use orgams to reinforce the behavior he wanted to see. It was enjoyable (it was sex after all), but part of him wanted to control that aspect of the hunter as well. A good bitch would listen and make Crowley's pleasure priority number one and his own pleasure second. 

So he started simply at first. When they fucked he would get himself off and leave the hunter desperately cring out for more. He didn't let Robert cum until he had reached his second orgasm deep in that ass. He did it that way for over a week and then he pushed it to one orgams for every three he received, usually broken up over several sessions throughout the day. Robeet would try and touch himself during or after it and it always got his ass a good hard spanking that reverberated through the house.

They progressed like that until Bobby bo longer knew when he was going to receive his next orgasm. Sex had shifted from a way to get off to a way to please Crowley, and that brought with it a new kind of pleasure. Pride, pride at knowing he was able to do his job and keep his priorities in line.

Crowely still let him cum about once a week but he always wanted to prologue it longer so he would watch those plump balls swell bigger from neglect. They filled his jockstraps better and would hang low whenever he was naked, out and vulnerable to the world.

The next step after limiting orgams was controlling them. Specifically making it to where Robert could cum untouched every single time, and if he failed to do it untouched he wouldn't get to cum at all. He did this by shoving a massive vibrator up into that ass at full power until he was spewing all out, it always involved sucking off Crowley to hammer in how his please was more important than Robert's. It doubled as trading for when to swallow and when not to. Sometimes he like knowing Robert could take all of him down and others he wanted to watch it spill from his lips and get stuck in his beard as it dripped out of him.

The vibrator had its setting lowered until it was on the lowest possible setting and Robert still came on it, training his hole to be extra sensitive so it could feel every bump and vein along that cock as it fucked him. Occasionally he didn't even have the hunter give him a blowjob, just had him keep that hard cock warm inside his mouth with his nose buried deep into his pubic hairs, wanting the man to associate his musk with getting off. Knowing that Crowley's cock was what gave him please and making him focus on that.

His effort gave him a desperate hunter who could cum on his cock regularly without even laying a finger on his dick. He even managed to get him to stop trying to get off in secret because Crowley always found him and punished him for disobeying orders. The issue arose when he found that Bobby was once again coming each and everytime they had sex. He still understood that sex was for Crowley more than it was for him but he was so sensitive that the rough fuckings he recieved always resulted in him spurting out under him.

The trading resumed with a cock ring to aid him in his plight. Robert would beg for him to remove it and he was always shushed and told that he would get to cum when it was time. This took by far the longest of any of the training sessions around orgasms. Time and again he would remove the cock ring to fuck Robert and see if he could learn to do it on command. He failed to restrain himself repeatedly, and received numerous spankings as a result. Whenever Bobby managed to go through several rounds without cumming Crowely had to use the vibrator again to check that his sensitivity was high enough. 

It was a long, slow process filled with many tears and apologies from Robert but eventually everything fell into place. He treasured the memory of their first time successfully doing it, he had been pounding that rump fiercely and screamed for the hunter to cum onto the sheets moaning his name. It was only the first time and he repeated it again and again sometimes commanding him to cum and other times not to make sure he could do it regularly. In the end he was successful and Robert could cum on command the vast majority of the time. On of the best times had been when he had Robert sit on his lad and his cock had just grown hard pressed between them, and he put his mouth up against that ear and whispered for him to cum. The man stiffened and a little bit spurted out from his dick. He was able to achieve an orgasm so soon after going hard because his entire body knew who was in control of it and it listened well.

....

(Sleeping)

It had been two solid weeks without a single orgasm for Robert and he had no intention of changing that. He planned on keeping him stopped up and letting his balls grow nice and plump, after which he would fuck the man for hours on end forcing every single drop out of him until he passed out from it.

He was spending the night staring at that body like he did most nights since he didn't require sleep but sometimes chose to indulge in it. Robert was laying on his side facing away from Crowley, he made it a rule that Robert wasn't allowed to sleep on his back because it obscured his view of that arse and that simply wouldn't do. It was a normal night until he heard desperate moans coming from that sleeping form next to him.

"Oooooh, Crowely, please." Crowely sat up and gazed over him to see his hard cock sticking up and glistening from the head. "Please let me cum. I'll be good." His hunter was so desperate that he was having a dream about him. 

He let the man continue on and on expecting him to climax across the bed spread at any moment but he never did. Even after thirty solid minutes the man was still just withering and moaning on the bed. He grew more wanton as it went on but he couldn't seem to climax from his wer dream. He decided to test something.

"Robert cum now." He was using his authoritative tone that always made Bobby obedient and he saw the immediate reaction of his cock spurting out from the head as he himped the air. He had made the men so desperate that even unconscious he was unable to climax unless he was given permission. He was absolutely perfect.

Crowley decided that he would celebrate by making tomorrow the day he ruined Bobby. He was going to get fucked on the bed, in the shower, over his desk, against the kitchen counter, on the back porch and so much more. He planned on having Bobby cum inside a jockstrap and then using that as a gag while he fu led him again. Somewhere in the day he would be riding a dildo while sucking off the demon and he wanted to fill him from both ends with his semen and then watching it drip out across his body.

....

(Wax)

Bobby was laid out on his stomach on the couch because Crowley wanted to fuck him in every room of the house so no matter where he was he would be reminded of the pleasure Crowley could bring him. He had a large ball gag between his teeth and was completely naked, lacking even a jockstrap to cover himself. Crowely stood over him with a candle half burnt and full of melted was. He gently tipped it over and let it drip onto that exposed hole. There was a moan as the hot liquid came into contact with his rim but Bobby had made no physical move to cover himself or impede the demons actions. The was continued to fall until he was completely covered in a thick layer of wax that had hardened and cooled into place. Without warning the was was ripped off of him and he howled behind his gag as he fisted the pillow of the couch between his fingers. This was his punishment for attempting to dress himself when he went out to get the mail which went against Crowley's rules. He slipped on a jockstrap instead of going out bottomless and when he returned he received a harsh punishment with a belt and Crowley explained he had a second punishment in store for him. That turned out to be the was and he was going to repeat it three more times to make the lesson stick.


	3. Still more smut.

**Summary for the Chapter:**

> The title says it all.

(Going Shopping)

He loved every aspect of his dear Robert. Namely his physical appearance and his personality, and since he had gotten rid of all his pesky inhibitions he loved the man all the more. Obedience was a great look for a man so set in his ways and sure of himself. He had ceased his challenges to Crowley's authority while still retaining his adorable sass and snark. Same Robert Singer but in a sluttier more obedient package.

It had been a pleasant evening where he was cooking dinner that he realized he needed a few things but rather than simply creating them or getting them himself, he wanted to send Robert out into public to get them. Robert had gone out numerous times since the shift in their relationship but he had always left in something similar to his normal wardrobe. Now he wanted to send him out to do his shopping

Not in Souix Falls, he didn't need to draw any unnecessary attention to them. No he'd take them to some store several towns over, one with plenty of onlookers to see Robert dressed so scantily but still far enough that no one would recognize him. There were so many options on how to dress the hunter and this wasn't likely to be something he could repeat, so he would need to milk the situation for all it was worth.

He spent the remainder or his time cooking dinner multi tasking and deciding on what exactly he would have Robert wear tomorrow. He didn't bother to make the spice he needed to make the meal taste right, wanting to sell the necessity of then going out and buying it. It was unnecessary as Robert was wrapped around his finger and would do whatever was asked of him. He could be told to go fuck himself on a dildo by the mailbox and he would (Crowley had him repeat the exercise numerous time, enjoying each instance of it).

That night as he fucked his love into submission his thoughts drifted to the scandalous possibilities of tomorrow. Not to say he didn't enjoy any opportunity to pound that fat ass and watch it jiggle with the large man moaning underneath him, but he was able to revenge Robert's body each night while it wasn't everyday he was able to expose him to the world. He made sure that the hunter was fucked thoroughly but didn't have the chance to get an orgasm. Crowley had been letting the man get ownt up for some time and tomorrow would be the perfect opportunity to set him off.

Before the sun had a chance to rise above the horizon Crowley positioned Robert over his lap with that fine hairy rump of his on display for his morning spanking. Daily punishments were essential to maintain the balance of their relationship, and to keep that large ass a wonderful shade of red. The intensity and number of hits was determined by how much the color had faded from the previous day. Sometimes on a few hard smacks were needed to get it to his desired color and other he gave it a full out assault that left the man begging to cum the end. However, he never begged for it to stop, he had learned that spanking was needed and thus halted all objections to the act early on.

He decided on twenty for today but before he carried out his punishment he admired the globes of that ass. It was massive, even bigger than it had been when they had started dating. This was thanks to the mandatory squats Crowley had him do each morning after his shower, as well as Crowley's own teasing and constant massaging of the muscles to make them swell up. His Robert now had a bubble butt (a term Crowley had always found too childish to describe something like this but it was an accurate description) that would shake and ripple as the slightest contact while still being firm underneath.

He ended his admiring to get started with the wake up call. The pleasant snores from Robert were nice but he had plans for the day and he needed to get started if he wanted things to so smoothly.

Slap one had him waking up with bleary eyes. Robert always woke up confused, not a good trait for a hunter but it made Crowley happy. He was able to see the man slowly gain cognition as his ass was beaten. Slap four started the rutting of that hard cock against his thigh. Slap 6 gave vocal cries of desperation. Slap 13 was when he began to arch his back and display his ass even more. On slap 20 his ass was tinged that deep scarlet he liked to keep it as and it was making Crowley wonder about letting his ass burn in the sun again, but that was for another day. He was busy with another scheme at the moment.

"Alrighy Robert it's time for you to get up and get yourself ready." He lightly patted that burning rump of his and recived a moan when the hunter got off of him, his cock flushed and hard. "Once you're done in the bathroom come out here for your morning squats, and then you'll need to get dress for what were doing today."

"Are we heading out for something?" He wasn't questioning Crowley's authority just following his normally curios nature. He wasn't just a researcher because it was helpful to hunters he also did it because he had an inner desire to learn more.

"Yes, love. There's some shopping I need to do and it will be much faster with your help. I'll get some clothes picked out while your getting clean okay."

"Okay." He walked into the bathroom giving Clowley an unobstructed view of his red rear end as he walked over to it. The sight was why Crowley always used his hand to deliver punishments instead of a belt or a paddle. For all the things he did to that sinful body he couldn't bring himself to scar the hunter there. His ass was about the only part of his skin that lacked any bullet or stab wounds and he didn't want to disrupt it with uncomfortable welts. He also wouldn't be able to fucke the counter so soon after punishment if sores formed on his skin.

He restrained himself from entering the bathroom to watch as Robert completed his morning routine. The image he made while administering his own enema was absolutely pornographic but Crowley didn't want to spoil his fun early. The pay off was always worth more when he denied himself until the end. So he sat and waited, when the shower could be heard running he got into action at a somewhat languid speed, he still had a good twenty minutes of time before Robert would be back in the bedroom so he lacked a reason to rush himself. 

He set about creating the perfectly tailored garments. He could easily make clothes that fit snugly but to make something that conformed precisely to one specific form required more effort and time to complete. He had made the finishing touches as the door to the bathroom swung open and the last remaining bits of steam dispersed into the air.

"Good, now that your clean you can start getting dressed." He reached his hand out with a black jockstrap in his grip. "Put this on and do your squats, only fifteen today since you'll be doing some work later and you need to have plenty of energy for that."

Bobby took the offered item and slipped in into place. The waistband was nice and thick to sit right above the curve of his ass and frame it along with the straps. He was no stranger to jockstraps at this point but these hung low in the front while still sitting high on his ass. He spread his legs shoulder width apart and started his set of 15 squats. 

Truthfully he'd always hated squats. They were his least favorite exercise seconded only by push ups, but he understood the need for them and he could tell his ass was bigger from them. But understanding the benefits he was getting from them and actively enjoying them in the moment were two entirely separate things. Crowley must have been enjoying himself, as he saw those cheeks spread to reveal that freshly stretched hole. Surprisingly the demon made no sounds or comments at the action, had Bobby looked behind him he would have know that Crowley was palming at himself in silence while seated on the edge of the bed, but with his back turned the hunter was none the wiser.

At the end of his fifteenth squat he stood and turned, feeling the burn in his legs from even the minimal exercise. The king of hell had managed to compose himself by that time and now stood in one of his suits looking as pissed off at the world as he did on any other day of existing.

"Come here for a moment so I can help you with this next part." He crossed the room and stood there until Crowley made a gesture with his hand for him to turn around. The light thud from the demon dropping to his knees was audible, and he felt one of the cheeks of his ass being pulled to the side before there was a presence pushing against his rim. Having been stretched so recently it was easily addled to enter him once more force was applied, but he was confused when he could feel a part of it go along his crease and slip under his jockstrap to rest eight behind his balls. "Crowlet, what is this?" "Its a special dueal vibrator that can torment you from both inside and out." The grin on his face carried into his tone and Bobby chose not to respond for fear of making a fool of himself at the concept.

"Okay your clothes are on the bed for you. Get dressed and meet me downstairs once you're finished with that." He stepped away from the bed and walked out the door leaving Robert in silence.

Approaching the bed Bobby found the three pieces of clothing he was supposed to wear. A black tank top that had been cut open on the sides and thinned out in the center to reveal more skin, as well as some blue camo compression shorts. They were made to be worn under regular exercise shorts but they would still cover all the necessary parts of him.

The shirt (if you could really call it that with how little of it there was) was solid black with some sort of design on the front but it was indiscernible in its current state. Slipping it over his head revealed just how minimal the fit. The thing straps went over his shoulders right beside his neck and the fabric of it covered his spine and right down the center of his chest and stomach. It was about two or three inches of coverage and it was loose fitting so it would hand and shift across his body if he were to bend over. His entire chest was out side from where his pecs met in the center, leaving his antipossesionn tattoo and swollen nipples visible. It continued down his torso, being just enough to fall over his belly button named navel, but not much else on the sides. At the bottom it looped around to the sides and rasted high on his hips as to not cover his ass or crotch. If he had more time Bobby would have looked in a mirror to see himself.

Next he put on the shorts. It took some effort to inch the fabric up his legs, and he could feel it pinching into his skin. The material was made to stretch snuggly over skin and it would be stretching a fair amount given the struggle to just get it up. Ultimately he did get it up and over his ass. The elastics band was set on top of the band of his jockstrap but no matter what he did a part the jockstrap would always sit above it and be visible. The bottom of the shorts came up to four inches above his knees, which was a bit of skin to expose but nothing Crowley hadn't seen before and it would still be decent in public. It would get him double takes from anyone he passed by but it was entirely legal. He was glad to have the jockstrap on because it shaped his package to bot poke against the front of it. It still emphasises him and pushed him forward but you couldn't easily see the outline of his dick, and he assumed the plight was equally well hidden from view.

He left his bedroom and went to meet Crowley in the kitchen. The demon was sitting st the table sipping at some tea whit a coffee mug and a single biscuit sat at the place across from him. Bobby took the open seat (the plug barely even registered to him, having grown used to having something up inside his hole) and took a sip from the mug. The coffee was strong with just a pinch of cream, exactly how he liked it to be.

"So what do we need to do today?" He picked up the biscuit and schooled his grimace. They weren't bad when Crowley made them but he made then what he deemed the proper was and that mean being extremely dense and thick. It would certainly appeal to someone's tastes but it wasn't Bobby's preferred way of having them.

"Yes I need to get a few things and it will be faster if you can grab a few groceries while I'm busy. We need a few spices that we've recently run out of."

"Is that why dinner was so bland last night. You did the best that you could with what you had but if you're missing an important ingredient it wont taste right no matter what you do."

He couldn't even be mad because Robert was trusting his judgment and had yet to question why he hadn't simply created the needed items. "I understand. We'll need to leave soon if we want to get there in time. It's a bit of a drive because they don't have everything we need in town so we'll just head somewhere else and do it there." Robert nodded as he finished his biscuit. "We can leave as soon as you're finished."

Bobby had swallowed the rest of his biscuit and washed it down with the remainder of his coffee before responding. "Sounds good, but do you want me to drive us there or are you driving?"

Crowley hadn't even let the thought cross his mind. He assumed he would be driving them there (Bobby liked driving over teleportation for domestic uses, it was a small preference that Crowley had no issues honoring). When he was thinking about his plan the drive there had always been a sort of deal with it later problem, but with this suggestion it made things all the sweeter. From the passengers seat he would be able to focus all his attention on Robert, and it meant he could add even more to his torment.

"You'll be driving love. Now your shoes are by the door. I'll get your plate for you." They went their separate ways and by the time they had reconvined at the front door Robert was already in his black close toed sandals. The hunternlooked ready to go but there weren't ready just yet.

"There's just one more thing Robert and then we can leave." He reached into the pockets of his jacket and produced a small bottle of lotion and two alligator nipple clamps, making it appear as if this had been the plan the whole time even if it had only come to him in the last ten minutes. He didn't need to give Robert an explanation as to what they were for he had been subjected to them many times previously. He quickly squeezed some lotion onto his finger and rubbed it over each sensitive pink nub. Robert didn't react to harshly to it but he let out a pleasant moan when the clamps were put on and tightened.

They climbed into the 83 Chevy Malibu and were off.

"Alright here's the money for the spices I need, remember breadcrumbs, cumin, and sage. I'll be back in about half an hour to get you once I'm finished with my errands. And you can cum if you need to but don't touch yourself."

"Alright bye." Bobby had placed the money into a small pocket on the inside of husbshirt and entered the store. It was empty given it was a weekday so normal people were at lunch or work but he got a rush at the thought of the few bystanders there looking at him. Crowley had just removed his nipple clamps as he stepped out of the car and the demon moved to the driver's seat so they were exceptionally puffy and red. He needed a mirror to get a good long look at himself, besides he had the time, it wouldn't take thirty minutes to get three spices.

He made it to the mens wear section to see himself in one of the mirrors. On the way there he felt the plug begin to vibrate against hisbprostate and right behind his balls, suddenly he was a lot less sure of Crowley leaving him alone. Once he found the full body mirror he was in awe, he looked fucked out and ready to fucked again. He was a mess of skin on display and his hair was sticking up at odd angles.

When he turned he could see the massive swell of his ass in his profile. It wasn't just big, it also had the help of the jockstrap and compression shorts pushing it up. He grabbed it with his own hands and squeezed barely silencing the wanton sounds inside his throats.

He knew he was absolutely fucked when he felt the beginnings of an orgasm so soon into it.

**Notes for the Chapter:**

> Please leave comments

**Author's Note:**

> Well that was certainly a thing.
> 
> Comments if you would be so kind.


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